The house has been on the market before. In 2014, it was reportedly first listed for $26.5 million and it was subsequently discounted and delisted in the following years, listing records show. Most recently, at the end of October 2017, the house reappeared on the market asking $21.5 million, but “was deactivated until we made the price adjustment,” said listing broker Ronald White of Douglas Elliman, who is handling the sale with his colleague Paul Brennan.

“We wanted to make it attractive,” Mr. White said, adding that he thinks the price adjustment will attract both previously interested parties and new buyers alike.

Mr. Drexler, 73, paid $17 million for the Wainscott house in 2008, property records show. He used a limited liability company linked to J.Crew’s East Village headquarters for the purchase.

Located between Wainscott Pond and the Atlantic Ocean, the 3,500-square-foot home sits on 2.3 acres and comes with 315 feet of ocean frontage. It has three bedrooms, a chef’s kitchen, double-height ceilings, large picture windows, wraparound decks and a wooden boardwalk that provides private access to the beach and “sets a high benchmark in quality oceanfront living,” according to the listing.

There is no particular reason why Mr. Drexler is selling, according to Mr. White. “He and his wife are masterful in terms of taking houses and making new of them,” Mr. White said, and they spent around two-and-a-half years renovating the home. “Now it’s time for someone to enjoy it for themselves.”

The Hamptons property isn’t the only piece of real estate that the Bronx-born Mr. Drexler, who could not be reached for comment, has been trying to unload. His two Tribeca homes—a townhouse and an apartment—have been on and off the market for some time and were last asking $27.5 million and $19.95 million respectively, though neither are listed right now.